256-96-2

Basic information

• Product Name: Iminostilbene
• Synonyms: 2,3,6,7-Dibenzazepine;5-Azadibenzo(a,e)cycloheptatriene;5H-Dibenz[b,f]azepin;5H-Dibenzo(b,f)azepine;Dibenz(b,f)azepine;Stilbene, 2,2'-imino-;(-)-O-FORMYL-D-MANDELOYL CHLORIDE;R-FMOC
• CAS NO: 256-96-2
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24
• EINECS: 249-478-4
• Product Categories: Stilbenes (substituted);Heterocyclic Compounds;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks;N-Containing;Others;Pharmaceutical raw material;Aromatics, Heterocycles, Metabolites & Impurities, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 256-96-2.mol
• Article Data: 32

Chemical Properties

• Melting Point: 197 °C
• Boiling Point: 221 °C(lit.)
• Flash Point: >230 °F
• Appearance: yellow to orange/powder
• Density: 1.290 g/mL at 20 °C(lit.)
• Vapor Pressure: 4.81E-05mmHg at 25°C
• Refractive Index: n20/D 1.523(lit.)
• Storage Temp.: Refrigerator
• Solubility: dioxane: 50 mg/mL, clear
• PKA: 1.71±0.20(Predicted)
• Water Solubility: Soluble in ethyl acetate (25 mg/ml), water (partly), dioxane, chloroform, and DMSO.
• BRN: 1343358
• CAS DataBase Reference: Iminostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: Iminostilbene(256-96-2)
• EPA Substance Registry System: Iminostilbene(256-96-2)

Safety Data

• Hazard Codes: C,Xi,N,Xn
• Statements: 34-51/53-22-36/37/38
• Safety Statements: 26-36/37/39-45-61-27-24/25
• RIDADR: UN 3265 8/PG 2
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 256-96-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow to orange-yellow fine powder

Uses

Iminostilbene is mainly used as a pharmaceutical intermediate for the production of carbamazepine, Oxcarbazepine, and rhodium catalyst ligand. It is a metabolite of of carbamazepine which is used primarily in the treatment of epilepsy and neuropathic pain.

Application

Iminostilbene has good antioxidant effects. N-acetyl iminostilbene was synthesized by incubating iminostilbene (2.0020 g, 10.360 mmol) with acetic anhydride.

Preparation

iminostilbene synthesis: 10,11-Dihydro-5-dibenz(b,f)azepine [Iminodibenzyl, 494-19-9] as raw material was acylated by triphosgene, after bromination by bromine and dehydrobromination, reacted with sodium hydroxide in isopropanol to give Iminostilbene.

Definition

ChEBI: Iminostilbene is a mancude organic heterotricyclic parent that consists of a seven-membered nitrogen hetrocycle fused with two benzene rings. It has a role as a marine xenobiotic metabolite. It is a mancude organic heterotricyclic parent and a dibenzoazepine.

General Description

5H-Dibenz[b,f]azepine, a tricyclic amine with a seven-membered ring, is commonly known as iminostilbene. It is used as an intermediate or a starting material in the synthesis of many anticonvulsant drugs.It is also used as a starting material to prepare pharmacologically important dibenzoazepine-pyridazine derivatives and synthesize olefinic multidentate ligand, which is used to prepare Rh(I) complexes.

Biochem/physiol Actions

2-(Bromomethyl)naphthalene is a fluorescent alkyl bromide. It causes the esterification of free carboxyl groups formed at the surface of polyethylene terephthalate by enzyme hydrolysis. It acts as organic electrophile in the P4S10/acyloin reaction.

InChI:InChI=1/C14H11N/c1-3-7-13-11(5-1)9-10-12-6-2-4-8-14(12)15-13/h1-10,15H

Synthetic route

2-bromostyrene (2039-88-5) + 2-Chloroaniline (95-51-2) → dibenzoazepine (256-96-2)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; DavePhos In 1,4-dioxane at 110℃; for 6h; Inert atmosphere;	99%

N-acetyl iminostilbene (19209-60-0) → dibenzoazepine (256-96-2)

Conditions	Yield
With triethyl borane; sodium hydroxide In tert-butyl methyl ether at 80℃; for 6h; Inert atmosphere; Sealed tube;	99%
Stage #1: N-acetyl iminostilbene With Triethoxysilane; sodium triethylborohydride In tert-butyl methyl ether at 80℃; for 6h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 20℃; for 1h; chemoselective reaction;	99%
Multi-step reaction with 2 steps 1: potassium hydroxide; triethyl borane / tetrahydrofuran / 24 h / 100 °C / Inert atmosphere; Schlenk technique; Sealed tube 2: sodium hydroxide; water / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere; Schlenk technique; Sealed tube View Scheme

2-(2-phenylethenyl)benzenamine (13066-19-8) → dibenzoazepine (256-96-2)

Conditions	Yield
With phosphoric acid at 100 - 300℃; for 2h; Temperature; Reagent/catalyst; Inert atmosphere; Industrial scale;	98.9%

9,10-dihydrodibenzazepine (494-19-9) → dibenzoazepine (256-96-2)

Conditions	Yield
With 1-methyl-2-nitrobenzene; palladium on activated charcoal at 230℃; for 1.5h; Rate constant; Kinetics; Thermodynamic data; var. hydrogen acceptors (also without acceptor); ΔH(excit.), ΔS(excit.); var. temp. and time;	98.2%
With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In toluene at 120℃; under 9750.98 Torr; for 8h;	24%
Stage #1: 9,10-dihydrodibenzazepine With N-Bromosuccinimide Stage #2: With pyridine

N-benzyl-5H-dibenzoazepine (78943-58-5) → dibenzoazepine (256-96-2)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 35 - 40℃; under 1500.15 - 2250.23 Torr; for 5h; Autoclave;	97%

5H-N-benzyl-10,11-dihydrobenzazepin-10-one (10464-31-0) → dibenzoazepine (256-96-2)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In methanol at 45 - 50℃; under 7500.75 - 9000.9 Torr; for 5h; Autoclave;	94.5%
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol / 4 h / 40 - 45 °C 2: 5%-palladium/activated carbon; hydrogen / methanol / 5 h / 35 - 40 °C / 1500.15 - 2250.23 Torr / Autoclave View Scheme

5H-dibenz[b,f]azepine-5-carbonylchloride (33948-22-0) → dibenzoazepine (256-96-2)

Conditions	Yield
In acetonitrile electrolysis (Et4NClO4, Hg-dropelectrode);	92%

10-bromo-dibenz[b,f]azepine (75272-34-3) → dibenzoazepine (256-96-2)

Conditions	Yield
With tetraethylammonium perchlorate In water; N,N-dimethyl-formamide cathode: Hg, working potential: -1.85 V, charge: 2.0-2.1 F/mol, 4-5 h;	89%

carbamazepin (298-46-4) → dibenzoazepine (256-96-2)

Conditions	Yield
With tetraethoxy tellurium(IV) In tetrachloromethane for 3h; Heating;	85%
With hydrogenchloride In water for 12h; Reagent/catalyst; Darkness;
With carbon dioxide at 160 - 200℃;

1-phenyl-1H-indole (16096-33-6) → dibenzoazepine (256-96-2)

Conditions	Yield
With methanesulfonic acid at 90℃; for 7h; Temperature;	83.4%
With polyphosphoric acid at 100℃;	67%
With PPA at 75 - 85℃; for 55h; Mechanism; substituent effect discussed;	43%
With PPA at 75 - 85℃; for 55h;	43%
With methanesulfonic acid; phosphorus pentoxide In toluene at 120℃; for 6h;

1,2-Bis(5H-dibenzazepin-5-yl)ethan-1,2-dion (119872-39-8) → dibenzoazepine (256-96-2)

Conditions	Yield
In acetonitrile electrolysis (Et4NClO4, Hg-dropelectrode);	80%

10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol (4014-77-1) → dibenzoazepine (256-96-2)

Conditions	Yield
With toluene-4-sulfonic acid In toluene at 25℃; Dean-Stark; Reflux;	78%

5-Propa-1,2-dienyl-5H-dibenzo[b,f]azepine (152700-38-4) + 3,5-Dichloro-2,4,6-trimethyl-benzonitrile N-oxide (13456-86-5) → dibenzoazepine (256-96-2) + 5-[3-(3,5-Dichloro-2,4,6-trimethyl-phenyl)-4-methylene-4,5-dihydro-isoxazol-5-yl]-5H-dibenzo[b,f]azepine + 5-[(5S,6S)-3,9-Bis-(3,5-dichloro-2,4,6-trimethyl-phenyl)-1,7-dioxa-2,8-diaza-spiro[4.4]nona-2,8-dien-6-yl]-5H-dibenzo[b,f]azepine

Conditions	Yield
In tetrachloromethane for 2h; Heating;	A 48% B 30% C 12%

bromobenzene (108-86-1) + bicyclo[2.2.1]hepta-2,5-diene (121-46-0) + 2-bromoaniline (615-36-1) → dibenzoazepine (256-96-2)

Conditions	Yield
With palladium diacetate; caesium carbonate; triphenylphosphine In N,N-dimethyl-formamide at 105 - 130℃; Inert atmosphere;	45%

N-benzyl-5H-dibenzoazepine (78943-58-5) → 9-methyl-acridine (611-64-3) + dibenzoazepine (256-96-2) + pyrrolo<3,2,1-jk>carbazole (208-71-9) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Conditions	Yield
at 750℃; under 0.04 Torr; for 0.333333h;	A 2% B 20% C n/a D n/a

ethanol (64-17-5) + 5-Azidocarbonyldibenzazepin (116822-14-1) → acridine (260-94-6) + dibenzoazepine (256-96-2) + 1,2-Dihydrobenzimidazo<1,7-a,b><1>benzazepin-1-on (118794-84-6) + 5-(N-Ethoxycarbonylamino)-dibenzazepin (118794-86-8)

Conditions	Yield
Mechanism; Product distribution; Irradiation; photolyse reactions with different alcohols and CH3CN as educts to different products, also with other reagents; also thermolysis reactions;	A n/a B n/a C n/a D 10%

N-methyldibenzazepine (52249-32-8) → dibenzoazepine (256-96-2)

Conditions	Yield
With 5,10,15,20-tetraphenyl-21H,23H-porphine iron(lll) chloride; sodium dithionite; air; tetramethyl ammoniumhydroxide In methanol; dichloromethane; water for 0.333333h; Ambient temperature;	170 % Chromat.

9,10-dihydrodibenzazepine (494-19-9) → acridine (260-94-6) + 9-methyl-acridine (611-64-3) + dibenzoazepine (256-96-2)

Conditions	Yield
iron(III) oxide at 550℃; for 1h; Product distribution; selectivity, activity of catalysts, variation of catalyst and temperature;	A 20.0 % Chromat. B 5.9 % Chromat. C 40.8 % Chromat.
manganese(III) oxide; magnesium oxide; potassium carbonate; tin(IV) oxide at 550℃; for 6h; Title compound not separated from byproducts;

diphenylamine-2,2′-dicarboxaldehyde (49579-63-7) → dibenzoazepine (256-96-2)

Conditions	Yield
With hydrazine hydrate In acetic acid for 2h; Heating;	3.8 g

C34H26N2O2 (107185-55-7) → acridine (260-94-6) + dibenzoazepine (256-96-2)

Conditions	Yield
In ethanol Quantum yield; Irradiation;

C34H28Cl2N2O2 (117176-56-4) → acridine (260-94-6) + dibenzoazepine (256-96-2)

Conditions	Yield
In ethanol Quantum yield; Irradiation;

9,18-diacetyl-4b,4c,9,13b,13c,18-hexahydro-tetrabenzo[b,f,b',f']cyclobuta[1,2-d;3,4-d']bisazepine (41217-00-9) → acridine (260-94-6) + dibenzoazepine (256-96-2)

Conditions	Yield
In ethanol Quantum yield; Irradiation;

9,18-dipropionyl-4b,4c,9,13b,13c,18-hexahydro-tetrabenzo[b,f,b',f']cyclobuta[1,2-d;3,4-d']bisazepine (41217-01-0, 52646-98-7) → acridine (260-94-6) + dibenzoazepine (256-96-2)

Conditions	Yield
In ethanol Quantum yield; Irradiation;

9,18-dibenzoyl-4b,4c,9,13b,13c,18-hexahydro-tetrabenzo[b,f,b',f']cyclobuta[1,2-d;3,4-d']bisazepine (41217-03-2, 52647-00-4) → acridine (260-94-6) + dibenzoazepine (256-96-2)

Conditions	Yield
In ethanol Quantum yield; Irradiation;

9,10-dihydrodibenzazepine (494-19-9) + 1-methyl-2-nitrobenzene (88-72-2) → dibenzoazepine (256-96-2) + o-toluidine (95-53-4)

Conditions	Yield
palladium on activated charcoal at 230℃; Kinetics; Rate constant; other hydrogen acceptor, var. temp., var. solvents;

9,10-dihydrodibenzazepine (494-19-9) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7) → dibenzoazepine (256-96-2) + (E)-1,2-diphenyl-ethene (103-30-0)

Conditions	Yield
palladium on activated charcoal Kinetics; Rate constant; Thermodynamic data; var. temp, ΔH(excit.), ΔS(excit.);

diphenylamine-2,2'-dicarbonyl chloride (32621-46-8) → dibenzoazepine (256-96-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / Palladium-Barium sulphate; Quinolin sulphate / xylene / 2.5 h / Heating 2: 3.8 g / Hydrazine hydrate / acetic acid / 2 h / Heating View Scheme

Vanadox (579-92-0) → dibenzoazepine (256-96-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 11.8 g / Thionyl chloride; Pyridine / 5 h / Heating 2: H2 / Palladium-Barium sulphate; Quinolin sulphate / xylene / 2.5 h / Heating 3: 3.8 g / Hydrazine hydrate / acetic acid / 2 h / Heating View Scheme

dibenzoazepine (256-96-2) + benzyl bromide (100-39-0) → N-benzyl-5H-dibenzoazepine (78943-58-5)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 48h;	100%
In dimethyl sulfoxide for 1.5h;	35%
With sodium hydroxide; Aliquat 336 In dichloromethane at 20℃;	32%

dibenzoazepine (256-96-2) + acetyl chloride (75-36-5) → N-acetyl iminostilbene (19209-60-0)

Conditions	Yield
Stage #1: dibenzoazepine With sodium hydride In N,N-dimethyl-formamide; mineral oil Inert atmosphere; Stage #2: acetyl chloride In N,N-dimethyl-formamide; mineral oil at 23℃; for 1h; Inert atmosphere;	100%
In toluene at 80℃; for 2h; Inert atmosphere;	93%
In toluene at 80℃; for 2h; Inert atmosphere;	93%

dibenzoazepine (256-96-2) + allyl bromide (106-95-6) → 5-allyl-5H-dibenzo[b,f]azepine (74074-19-4)

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane; water for 48h;	100%
Stage #1: dibenzoazepine With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 0.25h; Stage #2: allyl bromide In water; toluene at 20 - 55℃; for 4h;	95%
In dimethyl sulfoxide for 1.5h;	46%
With potassium carbonate In methanol for 5h; Heating;
With sodium hydroxide; N,N-didecyl-N,N-dimethylammonium bromide In toluene at 55℃; for 4h;

dibenzoazepine (256-96-2) + chloroacetyl chloride (79-04-9) → 2-chloro-1-(5H-dibenzo[b,f]azepin-5-yl)ethan-1-one (41216-96-0)

Conditions	Yield
With N,N-dimethyl-aniline In tetrahydrofuran for 1h; Heating;	100%
In benzene for 3h; Heating;	94.3%
In toluene at 90℃; for 4h; Inert atmosphere;	88%
With pyridine In acetonitrile at 20℃; for 24h; Acylation;	80%
In toluene for 12h; Heating;

dibenzoazepine (256-96-2) + 3-bromo-9H-carbazole (1592-95-6) → N-[3-(9H-carbazolyl)]iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	100%

dibenzoazepine (256-96-2) + tert-butyl 6-oxohexylcarbamate (80860-42-0) → (Z)-tert-Butyl 6-(5H-dibenzo[b,f]azepin-5-yl)hexylcarbamate (960129-50-4)

Conditions	Yield
With dibutyltin chloride; HSiPh3 In tetrahydrofuran at 20℃;	99%

dibenzoazepine (256-96-2) + mesitylene-2-carboxylic acid chloride (938-18-1) → 5-(2,4,6-trimethylbenzoyl)-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: dibenzoazepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: mesitylene-2-carboxylic acid chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	99%

bromobenzene (108-86-1) + dibenzoazepine (256-96-2) → N-phenyldibenzazepine (78943-59-6)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	99%
With nickel(II) oxide; potassium tert-butylate; triphenylphosphine In tetrahydrofuran at 100℃; for 24h; Inert atmosphere; Sealed tube; Green chemistry;	85%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Reagent/catalyst; Inert atmosphere;	71%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	71%
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; Buchwald-Hartwig Coupling; Inert atmosphere;

dibenzoazepine (256-96-2) + 2-Bromobiphenyl (2052-07-5) → N-(2-biphenyl)iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	99%

dibenzoazepine (256-96-2) + o-trifluoromethylphenyl bromide (392-83-6) → N-[2-(trifluoromethyl)phenyl]iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane for 16h; Inert atmosphere;	99%

dibenzoazepine (256-96-2) + 1-Bromo-4-fluorobenzene (460-00-4) → 5-(4-fluorophenyl)-5H-dibenzo[b,f]azepine (1414856-37-3)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	99%

5-bromo-1H-indole (10075-50-0) + dibenzoazepine (256-96-2) → N-(3-indazolyl)iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	99%

dibenzoazepine (256-96-2) + hexanoic acid (142-62-1) → C20H23N*ClH

Conditions	Yield
Stage #1: hexanoic acid With sodium tetrahydroborate In toluene at 0 - 5℃; Stage #2: dibenzoazepine With sodium tetrahydroborate In toluene at 25 - 80℃; for 4h; Stage #3: With hydrogenchloride In water; isopropyl alcohol	99%

dibenzoazepine (256-96-2) + 2,2-dichloropropane (594-20-7) → C17H17N

Conditions	Yield
Stage #1: dibenzoazepine With C29H35Br2CoN3; zinc dibromide; zinc In tetrahydrofuran at 22℃; for 0.25h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; Stage #2: 2,2-dichloropropane In tetrahydrofuran at 22℃; for 24h; Simmons-Smith Cyclopropanation; Inert atmosphere; Glovebox; regioselective reaction;	99%

dibenzoazepine (256-96-2) + 5-(cyano)dibenzothiophenium triflate → 5-cyanodibenzazepine (42787-75-7)

Conditions	Yield
With caesium carbonate In dichloromethane at 20℃; for 6h; Inert atmosphere;	99%

dibenzoazepine (256-96-2) + sodium isocyanate (917-61-3) → carbamazepin (298-46-4)

Conditions	Yield
In water; acetic acid at 15 - 60℃; for 4h; Product distribution / selectivity;	98.8%
In acetic acid at 18 - 60℃; for 5h; Product distribution / selectivity;	95.9%
In ethanol; acetic acid at 60 - 80℃; for 1.5h; Product distribution / selectivity;	93.7%

dibenzoazepine (256-96-2) + benzoyl chloride (98-88-4) → (5H-dibenzo[b,f]azepin-5-yl)(phenyl)methanone (41216-97-1)

Conditions	Yield
Stage #1: dibenzoazepine With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.25h; Stage #2: benzoyl chloride In dichloromethane at 20℃; Further stages.;	98%
In benzene	96%
In benzene for 3h; Heating;	85.6%

dibenzoazepine (256-96-2) + 2,4,6-trichlorobenzoyl chloride (4136-95-2) → 5-(2,4,6-trichlorobenzoyl)-5H-dibenz[b,f]azepine

Conditions	Yield
Stage #1: dibenzoazepine With potassium hexamethylsilazane In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: 2,4,6-trichlorobenzoyl chloride In tetrahydrofuran at 0 - 23℃; for 1h; Inert atmosphere;	98%

dibenzoazepine (256-96-2) + 2-Bromo-m-xylene (576-22-7) → N-(2,6-dimethylphenyl)iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%

dibenzoazepine (256-96-2) + chlorobenzene (108-90-7) → N-phenyldibenzazepine (78943-59-6)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Inert atmosphere;	72%
With potassium tert-butylate; copper(II) oxide In dimethyl sulfoxide at 80℃; for 18h; Solvent; Sealed tube; Inert atmosphere;	72%

dibenzoazepine (256-96-2) + 2-methylphenyl bromide (95-46-5) → 5-(o-tolyl)-5H-dibenzo[b,f]azepine (152019-98-2)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%

dibenzoazepine (256-96-2) + 9-bromophenanthrene (573-17-1) → N-(9-phenanthryl)iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%

1-bromo-4-methoxy-benzene (104-92-7) + dibenzoazepine (256-96-2) → 5-(4-methoxyphenyl)-5H-dibenzo[b,f]azepine (152019-82-4)

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	98%

2-bromo-1-benzothiophene (5394-13-8) + dibenzoazepine (256-96-2) → N-(2-benzothiophenyl)iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 80℃; for 16h; Inert atmosphere;	98%

2-chloropyridine (109-09-1) + dibenzoazepine (256-96-2) → 5-(pyridin-2-yl)-5H-dibenzo[b,f]azepine (1385022-02-5)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); 1-methyl-2-(2-(dicyclohexylphosphino)phenyl)-1H-benzoimidazole; sodium t-butanolate In toluene at 20 - 135℃; for 24h; Buchwald-Hartwig reaction; Inert atmosphere;	97%

dibenzoazepine (256-96-2) + 2,6-dimethyl-1-chlorobenzene (6781-98-2) → N-(2,6-dimethylphenyl)iminostilbene

Conditions	Yield
With C30H43O2P*C13H12N(1-)*CH3O3S(1-)*Pd(2+); lithium hexamethyldisilazane In 1,4-dioxane at 100℃; for 16h; Inert atmosphere;	97%

Upstream product

• 52249-32-8 N-methyldibenzazepine 
• 494-19-9 9,10-dihydrodibenzazepine 
• 75272-34-3 10-bromo-dibenz[b,f]azepine 
• 64-17-5 ethanol 
• 116822-14-1 5-Azidocarbonyldibenzazepin 
• 49579-63-7 diphenylamine-2,2′-dicarboxaldehyde 
• 33948-22-0 5H-dibenz[b,f]azepine-5-carbonylchloride 
• 119872-39-8 1,2-Bis(5H-dibenzazepin-5-yl)ethan-1,2-dion 
• 41217-00-9 9,18-diacetyl-4b,4c,9,13b,13c,18-hexahydro-tetrabenzo[b,f,b',f']cyclobuta[1,2-d;3,4-d']bisazepine 
• 41217-01-0 9,18-dipropionyl-4b,4c,9,13b,13c,18-hexahydro-tetrabenzo[b,f,b',f']cyclobuta[1,2-d;3,4-d']bisazepine 
• 41217-03-2 9,18-dibenzoyl-4b,4c,9,13b,13c,18-hexahydro-tetrabenzo[b,f,b',f']cyclobuta[1,2-d;3,4-d']bisazepine 
• 298-46-4 carbamazepin 
• 16096-33-6 1-phenyl-1H-indole 
• 88-72-2 1-methyl-2-nitrobenzene 

Downstream Products

• 70253-40-6 morpholinomethyl-2 5H dibenzoazepine 
• 79693-74-6 bis(morpholinomethyl)-2,8 5H dibenzoazepine 
• 33948-22-0 5H-dibenz[b,f]azepine-5-carbonylchloride 
• 42787-75-7 5-cyanodibenzazepine 
• 117600-91-6 (3aR,12bR)-1-(2,4-Dinitro-phenyl)-3-methyl-1,3a,8,12b-tetrahydro-1,2,8-triaza-dibenzo[e,h]azulene 
• 117600-88-1 (3aR,12bR)-3-Phenyl-1-p-tolyl-1,3a,8,12b-tetrahydro-1,2,8-triaza-dibenzo[e,h]azulene 
• 260-94-6 acridine 
• 885-23-4 9-acridincarboxaldehyde 
• 494-19-9 9,10-dihydrodibenzazepine 
• 21186-31-2 2-oxo-2H-dibenzazepine 
• 78943-58-5 N-benzyl-5H-dibenzoazepine 
• 86977-39-1 4-anisoyl-5H-dibenzazepine 
• 303-54-8 imipramine 
• 29883-11-2 N-(3-chloropropionyl)dibenzazepine 

Relevant articles and documents

Stability indicating spectrophotometric methods for quantitative determination of carbamazepine and its degradation product, iminostilbene, in pure form and pharmaceutical formulations

A stressed study on the stability and degradation behavior under ICH forced degradation conditions of most widely used antiepileptic drug; carbamazepine (CMZ) is presented in this work. The research also includes studying spectrophotometric nature of CMZ and assaying it with mostly used spectrophotometric techniques. Six simple and sensitive spectrophotometric methods are introduced as stability indicating methods for quantitative determination of CMZ and its degradation product, one of its reported potential impurities; iminostilbene (IMS). Dual wavelength is method I where two wavelengths (215 and 270 nm for CMZ and 258 and 307 nm for IMS) were chosen for each component while absorbance difference is zero for the second one. Method II is isoabsorptive point method where the absorbance of CMZ at A225 nm was measured in the range of 0.5–20 μg mL?1. Method III is second derivative method which allows simultaneous determination of CMZ at 247 nm and IMS at 273 nm without any interference. Method IV based on measuring the peak amplitude of first derivative of ratio spectra (1DD) at 280.5 and 253 nm for determination of CMZ and IMS, respectively. Method V is mean centering of the ratio spectra with good linearity for CMZ and IMS over 200–330 nm. Ratio difference method is method VI where good linearity was achieved for determination of CMZ and IMS by measuring differences in the amplitude of ratio spectra at 285, 258 nm and 258, 285 nm, respectively. The proposed methods show successful application in CMZ's pharmaceutical formulations.

Method for synthesizing iminostilbene

The invention discloses a method for synthesizing iminostilbene, which comprises the following steps: by using 1-phenylindole as a starting raw material, carrying out intramolecular rearrangement reaction on 1-phenylindole under the action of a composite acidic catalytic system to generate iminostilbene; wherein the composite acidic catalytic system is formed by mixing a phosphorus-containing acidic substance and a sulfur-containing acidic substance, the phosphorus-containing acidic substance is one or more of polyphosphoric acid, phosphoric acid and phosphorus pentoxide, and the sulfur-containing acidic substance is one or more of sulfuric acid, methanesulfonic acid and p-toluenesulfonic acid. The phosphorus-containing acidic substance and sulfur-containing acidic substance are used together to form the composite acidic catalytic system, the catalytic system is used in a reaction for catalytic synthesis of iminostilbene, corresponding reaction conditions are optimized, reaction time is shortened, side reactions are reduced, and therefore the method has the advantages of being high in product yield, short in reaction time and the like. The highest yield of the product reaches 83.4%, the purity is 99%, and a good technical effect is achieved.

Intermediate compound, carbamazepine and derivative thereof as well as preparation method of oxcarbazepine and derivative thereof

The invention provides an intermediate compound, carbamazepine and a derivative thereof as well as a preparation method of oxcarbazepine and a derivative thereof. 2-substituted aminophenylacetate or 2-substituted aminophenylacetonitrile and 2-halobenzonitrile are used as raw materials, substitution reaction, intramolecular condensation reaction, hydrolysis and hydrochloric acid acidification are carried out to obtain the oxcarbazepine and the derivative 5-substituent-10-oxa-10, 11-dihydro-5H-dibenzo [b, f] aza thereof, and the derivative of the oxcarbazepine can be used as a raw material to prepare the carbamazepine and the derivative 5-substituted iminostilbene thereof, an intermediate compound iminostilbene and intermediate compounds 5-substituted-10-methoxyiminostilbene and 10-methoxyiminostilbene. The raw materials used in the method are cheap and easy to obtain, and the cost is low; the preparation method is simple, conditions are easy to realize, the method is simple, convenientand safe to operate, and the process flow is short; the production amount of three wastes is small, and thus, the method is environmentally friendly; and a target product has high yield and purity, and is suitable for industrial production.